Cyclopropylphenol derivatives of the present invention are useful as intermediates of pharmaceuticals/agrochemicals and functional materials. For example, a 3-phenoxy-4-pyridazinol derivative having herbicidal activity is produced using a cyclopropylphenol derivative as an intermediate (Patent Document 1). Examples of known process for producing cyclopropylphenol derivatives include a process for synthesizing from styrenes by a Simmons-Smith reaction (Non-Patent Document 1), a process in which a 5-phenyl-pyrazoline is heated to reduce ring size (Non-Patent Document 2), a process in which an allyl phenol ether is subjected to an intramolecular ring closure by photoreaction (Non-Patent Document 3), a process for condensing a vinyl phenol ether and diazomethane using a palladium catalyst (Non-Patent Document 4), a process for coupling a hydroxy(cyclopropyl)boron complex, obtained by dihydroboronation of propagyl bromide followed by treatment with an alkaline aqueous solution, with a phenyl bromide using a palladium catalyst (Non-Patent Document 5), a process for synthesizing via an intramolecular ring closure by reacting 1-allyloxy-2-bromobenzene and t-butyl lithium (Non-Patent Document 6), a process for condensing cyclopropyl borate with a phenyl bromide in the presence of a palladium catalyst (Non-Patent Document 7), a process for synthesizing from (1,3-dibromopropyl)benzene by an intramolecular ring closure reaction using zinc (Non-Patent Document 8) and a process for reacting chloroform with a styrene in the presence of a phase transfer catalyst and sodium hydroxide (Non-Patent Document 9).
However, Simmons-Smith reagent, palladium catalyst and boron complexes are expensive reagents, and since intramolecular ring closure reactions by photoreaction or using t-butyl lithium, reactions for reducing ring size of pyrazoline using heat, cyclization reactions of dibromophenols using zinc or the like result in the formation of large amounts of by-products, the yield of the desired compound is generally low. Moreover, since Simmons-Smith reagent, diazomethane, boron complexes, t-butyl lithium and palladium catalysts and the like are unstable reagents, they have shortcomings such as problems with ease of the reaction procedure. In addition, in Non-Patent Document 8, a 4-(1,3-dibromopropyl)phenyl acetate derivative is synthesized by reacting a cinnamyl alcohol derivative and acetyl bromide, and then followed by an intramolecular ring closure reaction with zinc to synthesize a desired cyclopropylphenol derivative. However, cinnamyl alcohol is not acquired easily. In addition, in Non-Patent Document 9, dichloromethylcarbene is generated from chloroform by a styrene derivative to synthesize a dichlorocyclopropylphenol derivative. However, chloroform is highly toxic and it is difficult to acquire styrene derivatives.
[Patent Document 1] WO 03/016286 A1
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